Top Beach vacation packages in Eastern Massachusetts

Price found within the past 48 hours. Click for updated prices.

The Beachside

Nantucket Town

$1,352

per person

Dec 4 - Dec 6

found 1 day ago

Roundtrip non-stop flight included

Burlington (BTV) to Boston (BOS)

9.4/10 Exceptional! (397 reviews)

Very clean and comfortable room, friendly and helpful employees , and beautifully maintained grounds. Wonderful place to visit !

Reviewed on Oct 26, 2026

Harbor View Hotel

$1,675

per person

Nov 27 - Nov 30

found 18 hours ago

Roundtrip flight included

Miami (MIA) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

Loved the heated saltwater pool. Was disappointed there was not comfortable sitting in the room, esp on a rainy day or not feeling well, and watching a movie. Was surprised no elevator and we were on the third floor. The “grab and go” breakfast option was no more than a few pastries. That was disappointing. For early departure to catch ferry at 0530, no coffee was available.

Reviewed on Oct 22, 2026

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5* Beach vacations in Eastern Massachusetts

Price found within the past 48 hours. Click for updated prices.

Harbor View Hotel

$1,675

per person

Nov 27 - Nov 30

found 18 hours ago

Roundtrip flight included

Miami (MIA) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

Loved the heated saltwater pool. Was disappointed there was not comfortable sitting in the room, esp on a rainy day or not feeling well, and watching a movie. Was surprised no elevator and we were on the third floor. The “grab and go” breakfast option was no more than a few pastries. That was disappointing. For early departure to catch ferry at 0530, no coffee was available.

Reviewed on Oct 22, 2026

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3 Night Beach vacations in Eastern Massachusetts

Price found within the past 48 hours. Click for updated prices.

Harbor View Hotel

$1,675

per person

Nov 27 - Nov 30

found 18 hours ago

Roundtrip flight included

Miami (MIA) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

Loved the heated saltwater pool. Was disappointed there was not comfortable sitting in the room, esp on a rainy day or not feeling well, and watching a movie. Was surprised no elevator and we were on the third floor. The “grab and go” breakfast option was no more than a few pastries. That was disappointing. For early departure to catch ferry at 0530, no coffee was available.

Reviewed on Oct 22, 2026

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4 Night Beach vacations in Eastern Massachusetts

Price found within the past 48 hours. Click for updated prices.

By the Sea Guests Bed & Breakfast & Suites

$663

per person

Nov 26 - Nov 30

found 3 hours ago

Roundtrip flight included

Baltimore (BWI) to Boston (BOS)

9.2/10 Wonderful! (245 reviews)

excellent rooms are nice and spacious clean., shower was amazing, close to beach lovely views close to town

Reviewed on Oct 26, 2026

Harbor Hotel Provincetown

$15,715

per person

Jan 7 - Jan 11

found 1 day ago

Roundtrip flight included

Jacksonville (JAX) to Provincetown (PVC)

8.4/10 Very Good! (1,003 reviews)

Chatham Tides

$799

per person

Nov 26 - Nov 30

found 3 hours ago

Roundtrip flight included

Baltimore (BWI) to Boston (BOS)

9.4/10 Exceptional! (789 reviews)

The staff was extremely kind, room was warm, clean and the bathroom was extremely spacious. Perfect place in a perfect location.

Reviewed on Oct 25, 2026

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How do I book the best Eastern Massachusetts beach vacation packages?

Life’s a beach when you dive into our brilliant Eastern Massachusetts beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.

How can I find cheap beach vacations in Eastern Massachusetts?

A rental steps from the shore creates an amazingly affordable Eastern Massachusetts beach vacation. Seaside sojourns during low season start from $663. Prices and availability are subject to change. Additional terms may apply.

When should I book a Eastern Massachusetts beach holiday?

For a bustling beach break, book in . For a less crowded coast, is the time to turn up.

How can I book the best family beach vacations in Eastern Massachusetts?

With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.

How do I find a Eastern Massachusetts beachfront vacation?

Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.

Can I book a package including a Eastern Massachusetts vacation beach house rental?

Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.

Can I find Eastern Massachusetts beach vacation deals?

Sort your search results by deals to delight in amazing Eastern Massachusetts beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.

Can I book a Eastern Massachusetts beach trip with free cancellation and/or flexible dates?

Just like the Eastern Massachusetts tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.

Why should I book my Eastern Massachusetts beach vacation with Expedia?

Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Eastern Massachusetts. (OK, maybe not that last part.)

Top Beach Eastern Massachusetts Hotels

Sea Crest Beach Resort

350 Quaker Rd North Falmouth MA

2 hours drive from Fenway Park

At this hotel, get ready to enjoy the sunsets on the beach in North Falmouth, as you'll be near Cape Cod Beaches. 2 restaurants, a private beach, and a beach ...

7.6/10 Good! (541 reviews)

Travelers like: on the beach, sun loungers, beach bars, beach umbrellas

Travelers say...

"The hotel is amazing, very nice beach view and the staff is so friendly"

Reviewed on Oct 26, 2026

Lighthouse Inn

1 Lighthouse Inn Rd West Dennis MA

2 hours drive from Fenway Park

Make the most of this fantastic location, as you'll be a short walk from Cape Cod Beaches with a holiday at this hotel. Amenities at Lighthouse Inn include a ...

Chatham Bars Inn

297 Shore Rd Chatham MA

2 hours drive from Fenway Park

Settle in and relax at this luxury boutique resort and get ready to stroll along the shore in Chatham, as you'll be a short walk from Cape Cod Beaches. 3 outdoor ...

See all 15,936 properties in Eastern Massachusetts

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.